Trifluoroacetic acid → methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate

HRID 595113노트

반응식

HRID 595113 반응식
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[C:14]([O:15][CH2:16][CH:17]2[CH:21]=[CH:20][CH2:19][N:18]2C(OC(C)(C)C)=O)=[C:13]([C:29]([O:31][CH3:32])=[O:30])[C:12]([N:33](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[CH:11][CH:10]=1>C(Cl)Cl>[NH2:33][C:12]1[C:13]([C:29]([O:31][CH3:32])=[O:30])=[C:14]([O:15][CH2:16][CH:17]2[CH:21]=[CH:20][CH2:19][NH:18]2)[C:9]([Br:8])=[CH:10][CH:11]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86712822Tert-butyl 2-(6-bromo-3-[bis-(tert-butoxycarbonyl)amino]-2-methoxycarbonylphenoxymethyl)-2,5-dihydropyrrole-1-carboxylate2회

생성물 1

HCID 86712821methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate수율 88.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TFA (5 mL) was slowly added to a suspension of tert-butyl 2-(6-bromo-3-[bis-(tert-butoxycarbonyl)amino]-2-methoxycarbonylphenoxymethyl)-2,5-dihydropyrrole-1-carboxylate (Intermediate 19, 3.55 g) in DCM (5 mL). The resultant dark solution was stirred at room temperature for 3 hours. The volatiles were removed in vacuo and the residue was partitioned between ethyl acetate and saturated aqueous potassium carbonate solution. The layers were separated and the aqueous layer was extracted with more ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to give methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate (1.64 g) as a dark oil.

후처리

  1. customThe volatiles were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous potassium carbonate solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with more ethyl acetate
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fd2e6b58ce0f43baa74117bcaa278b47
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242997B2

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